Thionyl Chloride → HCID 178422749, compound

HRID 1898383Notes

Reaction equation

HRID 1898383 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24](O)=[O:25])=[CH:15][C:13]=2[N:14]=1.S(Cl)(Cl)=O.[C:31]([C:35]1[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=1)([CH3:34])([CH3:33])[CH3:32].CCN(C(C)C)C(C)C>C1COCC1>[C:31]([C:35]1[CH:36]=[CH:37][C:38]([NH:39][C:24]([C:16]2[C:17]3[O:21][C:20]([CH3:22])([CH3:23])[CH2:19][C:18]=3[C:12]3[NH:11][C:10]([NH:9][C:3]4[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])=[N:14][C:13]=3[CH:15]=2)=[O:25])=[CH:40][CH:41]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 698614-Tert-ButylanilineHCID 81531DiisopropylethylamineHCID 178422815HCID 178422815, compound

Product 1

HCID 178422749HCID 178422749, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following the procedure described for Example-108 using 2-[(2-chloro-6-fluorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-15, 0.100 g, 0.266 mmol), thionyl chloride (2.0 mL), 4-tert-butylaniline (0.079 g, 0.400 mmol), THF (10.0 mL) and DIPEA (2 mL). The obtained crude product was purified by column chromatography on neutral alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.055 g of the desired product. 1HNMR (DMSO-d6): δ 1.21 (s, 9H), 1.55 (s, 6H), 3.13 (s, 2H), 7.27-7.46 (m, 6H), 7.55 (d, J=8.7 Hz, 2H), 9.67 (s, 1H), 11.20 (s, 2H); MS [M+H]+: 507.50.

Workup

  1. customThe title compound was prepared
  2. customThe obtained crude product
  3. customwas purified by column chromatography on neutral alumina eluting with 0.7-1.0% MeOH

Sources & evidence

ORD record
ord-a0db54b0a9104e39a394df2da1feca56
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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